반응 #1960487

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7,8-difluorochroman-6-ol

1-(4-propylcyclohexyl)-prop-2-yn-1-ol

triphenylphosphine

DIAD

sodium chloride

→

7,8-difluoro-6-[1-(4-propylcyclohexyl)prop-2-ynyloxy]chroman

용매

THF

반응 조건

후처리

1. 1
   workup.ADDITIONare added over the course of 30 min with ice-
2. 2
   온도cooling
3. 3
   추출the mixture is extracted a number of times with MTBE
4. 4
   세척The combined organic phases are washed with water and saturated sodium chloride solution
5. 5
   기타the solution is dried
6. 6
   기타after removal of the solvents
7. 7
   기타is purified by column chromatography (SiO2, n-pentane:MTBE=2:1)

실험 절차

5.0 g (26.9 mmol) of 7,8-difluorochroman-6-ol are initially introduced in 65 ml of THF together with 5.33 g (29.6 mmol) of 1-(4-propylcyclohexyl)-prop-2-yn-1-ol and 8.45 g (32.2 mmol) of triphenylphosphine, and 6.79 ml (34.9 mmol) of DIAD are added over the course of 30 min with ice-cooling. After 19 h at RT, semi-saturated sodium chloride solution is added, and the mixture is extracted a number of times with MTBE. The combined organic phases are washed with water and saturated sodium chloride solution, and the solution is dried using sodium sulfate. The residue remaining after removal of the solvents is purified by column chromatography (SiO2, n-pentane:MTBE=2:1), giving 7,8-difluoro-6-[1-(4-propylcyclohexyl)prop-2-ynyloxy]chroman as a pale-brown oil.

출처